The Most Stylish Male Characters in Film – Beckett Simonon
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The Most Stylish Male Characters in Film

Menswear Knowledge Movies

Gordon Gekko – Michael Douglas in Wall Street

“... buy a decent suit. You can't come in here looking like that. Go to Morty Sills.
Tell him I sent you …”

It’s common to see a movie character boost an existing trend, but not so run-of-the-mill when a character creates one. Gordon Gekko is one of the latter—the timeless emblem of the American power look, wearing a striped suit with substantial shoulder pads, French cuffs, suspenders, and contrasting collars (the Gekko shirt, anyone?). His on-screen look created the favorite uniform of the real Wall Street yuppies during the 80s. Bold beyond limits, his entire look screams power. It’s not difficult to tell who the boss is when he’s wearing swag like that. No detail too small, everything in it’s place, showing-off at its best: a sartorial icon of American fashion for men.

Guido Anselmi – Marcello Mastroianni in 8 ½

“… What is this flash of joy that's giving me new life? Please forgive me sweet creatures; I didn't realize, I didn't know. How right it is to accept you, to love, you... and how simple”

One struggles to find a stronger reference to Italian tailoring in film. We are talking not only about Anselmi’s character, but about Mastroianni himself. Dressed-up to excellence, the man is a walking, talking example of finding a uniform that works well and sticking to it. Elegance never looked so simple yet so delightful—think of Mastroianni’s charm. This man represents Italian sartorial and meticulous attention to fit. His clothes are modest but powerful because they match his body in every way. Dark suit, white shirt and dark tie. Seems simple? Without his confidence and the perfect fit these clothes would be next to nothing. Did we mention the man dated Catherine Deneuve? The one and only Marcello Mastroianni.

Johnny Strabler – Marlon Brando in The Wild One

“… you think you're too good for me. Nobody's too good for me! Anybody thinks they're too good for me, I make sure I knock 'em over sometime …”

The Johnny Strabler look may go by unnoticed these days. Back in the day, however, it was the flag of youthful rebellion that led biker jackets to become the icon of masculinity and a wild spirit. Adopted by musicians and the young-at-heart, this look represented everything you stood for as a rebel. What’s amazing is that Brando’s character inspired a complete generation, one that contrasted with the etiquette pursued by most men at the time—all of them flaunting flawless posture the way their fathers once did. But Brando broke all the rules and carried a torch in name of the young, rebelling with his clothes but also with his attitude. Sure, it was defiant. But above all, stylish.

Frank Bullitt – Steve McQueen in Bullitt

“… look, you work your side of the street, and I'll work mine… you sell whatever you want, but don't sell it here tonight …”

It’s safe to say that a police lieutenant has never looked this good. The amazing look is the result of the very thin line between McQueen’s personal style and Bullitt’s wardrobe. He’s pure 60s cool at its best and a perpetual member of men’s style hall of fame. Layering was his game—Bullitt always seemed to be prepared for any weather, while looking assertive and cool. Every item in Bullitt’s outfit is a common staple in gentleman attire even today. But every menswear enthusiast knows there’s one garment that stands out—Bullit’s rust brown herringbone tweed jacket with suede elbow patches. We have one word for the 3-roll-2 buttons (top one hiding over the right lapel), the ticket pocket, the flaps, the double vents. It’s perfection.

Thomas – David Hemmings in Blow-Up

“… who says I can't? I'm only doing my job. Some people are bullfighters, some people are politicians. I'm a photographer … “

It’s just Thomas. No last name, and no nothing. Just a David Bailey-ish photographer living and working in vibrant London during the 60s. Blow-Up was the first of Antonioni’s films in English, and he made a sure bet by portraying Thomas with the authentic look and feel of London’s youth. Thomas’ appearance reflects the overwhelming allure and delight of the period. There’s something about simplicity and freedom in his style. White pants, a loose unbuttoned shirt and lace-less boots. He’s the epitome of effortless flair. We know what you are thinking—there’s also gorgeous Jane Birkin half-naked. Can’t get cooler than that.

Benjamin Braddock – Dustin Hoffman in The Graduate

“… For god's sake, Mrs. Robinson. Here we are. You got me into your house. You give me a drink. You put on music. Now you start opening up your personal life to me and tell me your husband won't be home for hours …”

Ivy leaguer Ben Braddock is the personification of classic leisurewear: great fitting sport jackets, crisp chinos, button-down shirts, laid-back polos, and timeless crewnecks. The man looked like he owned Scott Sternberg’s “Band of Outsiders”, with just a little extra dash of corduroy and despair and one nifty quarter-life crisis. But there’s something more to it. In addition to his unkempt look and undeniable sense of permanent angst, he always wore his immaculate white boxers. Such whiteness is the right amount of good when a man is having an affair with the wife of his father’s business partner. May the gods of Film bless Mrs. Robinson, queen of all MILFs. That’s how seducing a man should always be.

Richie Tenenbaum - Luke Wilson in The Royal Tenenbaums

“… I wrote a suicide note. - You did? - Yeah. Right after I regained consciousness …”

A tennis professional suffers a nervous breakdown and reunites with his completely dysfunctional family, while depressed and falling in love with his sister. Richie Tenenbaum’s character may sound absurd and well, frankly speaking, he actually is. Suffice it to say that his style is no different. Just think of the camel suit with the big-hearted lapels, the old-fashioned tennis shirt, the Bjorn Borg-inspired sweatband, the Vuarnet aviator sunglasses, the pet falcon and the seriously luxurious vintage luggage. The look sounds conflicting, at best, but Richie makes it appear very well put together and, honestly, it works like a charm. Now that’s what we call owning a style.

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